Enantioselective Conjugate Addition of a Lithium Ester Enolate Catalyzed by Chiral Lithium Amides

Mixed aggregates of chiral lithium amide and lithium ester enolate have been employed in the enantioselective conjugate addition on α,β-unsaturated esters. Michael adducts were obtained in ee's up to 76% combining a lithium enolate and a chiral 3-aminopyrrolidine lithium amide. The sense of the...

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Bibliographic Details
Published in:Organic letters 2006-12, Vol.8 (25), p.5745-5748
Main Authors: Duguet, Nicolas, Harrison-Marchand, Anne, Maddaluno, Jacques, Tomioka, Kiyoshi
Format: Article
Language:English
Subjects:
Amides - chemistry
Catalysis
Lithium - chemistry
Organometallic Compounds - chemical synthesis
Pyrrolidines - chemistry
Solvents
Stereoisomerism
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Summary:Mixed aggregates of chiral lithium amide and lithium ester enolate have been employed in the enantioselective conjugate addition on α,β-unsaturated esters. Michael adducts were obtained in ee's up to 76% combining a lithium enolate and a chiral 3-aminopyrrolidine lithium amide. The sense of the induction was found to be determined by both the relative configuration of the stereogenic centers borne by the amide and the solvent in which the reaction was conducted.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol062270d